Yellowish-brown vat dye.



' of 97 sulfuric acid, untilfa test *portiou UNITED STATES PATENT OFFICE.

, OSCAR BALLY AND HUGO WOLFE, 0F MANNHEIM, GERMANY, ASSIGNOR T0 BADISCHE I ANILIN & SODA FABRIK, OF LUDWIGSHAFEN-ON-THE-BHINE, GERMANY, A GOR- POBATION.

Specification of Letters Patent.

YELLOWISH-IBROWN VAT DYE.

No Drawing. Original application filed December 9, 1911, Serial No. 664,865. Divided and this application To all whom it may concern: I

Be it known that we, OSCAR BALLY and HUGO WOLFF, respectively citizen of the Swiss Republic and subject of the Grand Duke of Baden, residing at Mannheim, Germany, have invented new and useful Improvements in Yellowish-Brown Vat Dyes, of which the following is a specification.

The specification of Patent No. 1,016,604 describes the manufacture of coloring matters by condensing halogenated ketones anddiketones, such for instance. as benzophenone, benzil and phenanthraquinone, with amino compounds of the anthracene series, whereby coloring matters are obtained which dye cotton, from the vat, from red to violetbrown shades. Similar coloring matters canv be obtained by condensing. halogen deriva- Our'new coloring matter consists when ofiabrown powder which yields a redbrown solution in concentrated sulfuric acid and a brown' solution in 23% fuming sulfuric acid. It yields a red-brown vat in alkali hydrosulfite solution .and from this vat colors cotton red-brown shades which,

upon washing and drying, become very fast yellowish brown. n

- The followin example will serve to illustrate further t e nature of our invention,

which, however, is not confined to this exam ple. The parts are by weight.

and l-amino-anthraquinone, "and 375 parts shows that the reaction is complete." Pour cene series which can be obtained by heating filed January 23, 1915. Serial No. 4,030.

ated fiuorenone derivatives with amino-an thraquinones. i ,1

We have now found that the condensation product obtainable from the dihalogenfluorenone and two molecular proportions of l-amino-anthraquinone, on being treated with a dehydrating agent,'can be converted into a' new coloring matter which dyes on cotton from a vat fast yellowish brown shades. It is possible that during the react-ion the elemerfis of water are removed and inner condensation takes place, so that arcidin rings are formed. Thus the formation of coloring matter can probably berepresented by the following formulae the melt" into water, boil, filter oil and wash and dry the product which can be freed from any sulfonic acid by boiling itwith dilute caustic soda solution. The coloring matter, [which is thus obtained in the form of a brown powder, yields a red-brown solution in concentrated sulfuric ,acid and a brownsolution in 23% fuming sulfuric acid. With alkali hydrosulfite, it yields a red-brown vat and, from this vat, cotton is' colored redow what we claim is brown shades which, upon washing anddryin become very fast yellowinsh brown. Heattogether, at from to 165 0,25]. parts of the condensation product from- I dibrom-fluorenone- (see ,Berichte 38,-37651Y The new-coloring matter of the anthra 70;

with sulfuric acid the condensation product from dibrom-fluorenone' and l-amino-an- I thraquinone, which new coloring matter concentrated sulfuric acid and a brown soluprobably possesses a constitution corresponding to the formula and which consists, when dry, of a brown 15 powder which yields a red-brown solution in tion in 23% fuming sulfuric acid, which yields a red-brown vat in alkali hydrosulfite solution and from this vat colors cotton redbrown shades which, upon washing and drying, become Very fast yellowish brown.

In testimony whereof we have hereunto set our hands in the. presence of two subscribing witnesses.

OSCAR BALLY.

HUGO WOLFF.

Witnesses:

ARTHUR DENONVILLE, W. ERNST. 

